US5654345A - In situ blown foams - Google Patents

In situ blown foams Download PDF

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Publication number
US5654345A
US5654345A US08/501,691 US50169195A US5654345A US 5654345 A US5654345 A US 5654345A US 50169195 A US50169195 A US 50169195A US 5654345 A US5654345 A US 5654345A
Authority
US
United States
Prior art keywords
resole
foam
catalyst
reaction product
process according
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US08/501,691
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English (en)
Inventor
Vyacheslav S. Grinshpun
Byron Jeffrey Hulls
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Owens Corning Intellectual Capital LLC
Original Assignee
Owens Corning Fiberglas Technology Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Owens Corning Fiberglas Technology Inc filed Critical Owens Corning Fiberglas Technology Inc
Priority to US08/501,691 priority Critical patent/US5654345A/en
Assigned to OWENS-CORNING FIBERGLAS TECHNOLOGY INC. reassignment OWENS-CORNING FIBERGLAS TECHNOLOGY INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: GRINSHPUN, VACHESLAV B., HULLS, BYRON JEFFREY
Priority to EP96923411A priority patent/EP0785963A4/de
Priority to JP9505830A priority patent/JPH10505878A/ja
Priority to KR1019970701604A priority patent/KR970706341A/ko
Priority to AU63928/96A priority patent/AU6392896A/en
Priority to PCT/US1996/010798 priority patent/WO1997003115A1/en
Priority to CA002198629A priority patent/CA2198629A1/en
Publication of US5654345A publication Critical patent/US5654345A/en
Application granted granted Critical
Assigned to OWENS CORNING INTELLECTUAL CAPITAL, LLC reassignment OWENS CORNING INTELLECTUAL CAPITAL, LLC ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: OWENS-CORNING FIBERGLAS TECHNOLOGY, INC.
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/54—Polycondensates of aldehydes
    • C08G18/542—Polycondensates of aldehydes with phenols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
    • C08J9/06—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a chemical blowing agent
    • C08J9/08—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a chemical blowing agent developing carbon dioxide
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
    • C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2110/00—Foam properties
    • C08G2110/0025—Foam properties rigid
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2110/00—Foam properties
    • C08G2110/0041—Foam properties having specified density
    • C08G2110/005—< 50kg/m3
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2110/00—Foam properties
    • C08G2110/0083—Foam properties prepared using water as the sole blowing agent

Definitions

  • This invention relates to the low density microcellular, rigid foams made from low water content or waterless resins such as phenolic resin (resole or novalac). We make the in situ blown, closed cell foams without an external blowing agent.
  • Insulating synthetic foams have found various application in contemporary society.
  • One of the most voluminous applications of these foams is in the construction field, as insulators for walls, roofs, basements, etc. More Specialized applications for these foams include appliances (refrigeration), pipes, ducting, auto, aerospace and marine industries.
  • This invention forms in situ carbon dioxide blown closed cell insulating foams in which blowing is achieved by the evolution of carbon dioxide resulting from partial hydrolysis of isocyanates such as methyl diphenyl diisocyanate (MDI) by water in the resole.
  • the invention uses no additional blowing agent. The reaction is fast and the resulting product has small, closed cells that exhibit long term thermal performance.
  • composition comprises the following ingredients:
  • Catalysts such as stannous octoate.
  • the process for producing the closed cell insulating foam of the invention comprises mixing the resole, the surface active agent and the MDI at room temperature. Next, the catalyst is added and stirred vigorously. The prefoam thus formed is placed in a release paper lined steel closed mold preheated at 60° C., and the mold is maintained at this temperature for one minute. Finally, the foam bun thus produced is removed from the mold and allowed to cure at room temperature.
  • the catalyst is one or a mixture of dibutyltin dilaurate, N,N,N',N'-tetramethyl-1,3-butanediamine, stannous octoate acetate or triethylene diamine. After vigorous mixing for 15 seconds, the mixture is transferred to a closed mold at 25°-90° C. After 0.5 to 5 minutes of cure time, the product is removed from the mold.
  • the novalac product When the phenol is used in molar excess, the novalac product has little or no hydroxymethyl substitution and has the following formula: ##STR2## where X is hydrogen and n ⁇ 0, 1, 2, 3, or higher.
  • the --NCO containing compounds include the following: 2,4-tolylene diisocyanate; 2,6-tolylene diisocyanate; p-phenylene diisocyanate; polymethylene polyphenylisocyanate; diphenyl-methane diisocyanate; m-phenylene diisocyanate; hexamethylene diisocyanate; butylene-1,4-diisocyanate; octamethylene diisocyanate; 3,3'-dimethoxy 4,4-biphenylene diisocyanate; 1,18-octadecamethylene diisocyanate; polymethylene diisocyanate; benzene triisocyanate; naphthylene-2,4-diisocyanate, 3,3'-dimethyl-4,4'-biphenylene diisocyanate; 4,4'-diisocyanate; diphenylether; naphthylene-1,5-diisocyanate;diis
  • catalysts used for polyurethane formation are those known in the art and consist of tertiary amines, metal salts, or mixtures thereof.
  • suitable catalytic compounds are triethylamine, dimethylaminoethanol, N,N,N',N'-tetraethylethylenediamine, N,N,N',N'-tetramethyl-1,3-butanediamine, bis(-dimethylaminoethyl)ether, 1,4-diazol[2.2.2]-bicyclooctane, N-methyl- or ethylmorpholine, stannous oleate, stannous 2-ethylhexanoate, dibutyltin dilaurate, dibutyl-tin dilauryl mercaptide, dibutyltin diacetate, lead naphthenate, zinc stearate, or mixtures thereof.
  • the preferred catalysts for our invention are non-acidic organotin catalysts.
  • the particular organic structure for the organotin catalyst is not critical; it is only necessary that tin be present since the tin is the basic catalytic agent.
  • suitable organotin catalysts are stannous oxalate, stannous oleate, stannous chloride, stannous formate, etc. Any organotin compound which is not volatile or subject to decomposition at the initial reaction temperature (which is not higher than 90° F.) and which is soluble in the reaction mixture will suffice.
  • Preferred catalysts are reaction products of stannous oxide (SnO) or dibutyltin oxide with a carboxylic acid having 1 to 20 carbon atoms.
  • a preferred catalyst is stannous octoate (stannous 2-ethylhexoate) Sn(C 8 H 12 O 2 ) 2 -- which is a reaction product of stannous oxide and 2-ethylhexoic acid.
  • catalysts derived from dibutyltin oxide are dibutyltin diacetate, dibutyltin di(2,ethylhexoate) and dibutyltin dilaurate.
  • a surface active agent of an alkylene glycol of 2 to 10 carbon atoms such as ethylene glycol, butylene glycol and propylene glycol or an ether of an alkylene glycol of 2 to 10 carbon atoms such as diethylene glycol and dipropylene glycol, or mixture thereof.
  • the preferred surface active agent is a alkylene glycol-polyoxyalkylene block copolymer.
  • the key to this invention is a waterless or low water phenolic resin.
  • the resulting foam has a particular microcellular structure which provides high strength and interrupts crack migration.
  • This resol was analyzed by NMR and found to have 1.57 methylol groups per phenol.
  • Example II We used the resol of Example I to produce a low density closed cell structured foam having a small cell size and a rapid demolding time. We used the following ingredients and amounts.
  • the surface active agent used was an ethylene oxide propylene oxide block copolymer with a molecular weight greater than 5,000.
  • blowing agent No blowing agent was added to the mixture.
  • the only blowing agent present was the 5.4% water from the resol reaction.
  • the resulting foam has the following advantages: no blowing agent used (environmentally friendly); closed cell structure-long term thermal performance; economical--due to use of resol chemistry; fast urethane-type reaction; small cell size -80/ ⁇ k; microcellular structure in the struts; superior physicals at low density; and low flammability.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
US08/501,691 1995-07-12 1995-07-12 In situ blown foams Expired - Lifetime US5654345A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
US08/501,691 US5654345A (en) 1995-07-12 1995-07-12 In situ blown foams
AU63928/96A AU6392896A (en) 1995-07-12 1996-06-24 In situ blown foams
JP9505830A JPH10505878A (ja) 1995-07-12 1996-06-24 現場発泡フォーム
KR1019970701604A KR970706341A (ko) 1995-07-12 1996-06-24 현장 취입 발포체(in situ blown foams)
EP96923411A EP0785963A4 (de) 1995-07-12 1996-06-24 In-situ verschäumte schaumstoffe
PCT/US1996/010798 WO1997003115A1 (en) 1995-07-12 1996-06-24 In situ blown foams
CA002198629A CA2198629A1 (en) 1995-07-12 1996-06-24 In situ blown foams

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US08/501,691 US5654345A (en) 1995-07-12 1995-07-12 In situ blown foams

Publications (1)

Publication Number Publication Date
US5654345A true US5654345A (en) 1997-08-05

Family

ID=23994637

Family Applications (1)

Application Number Title Priority Date Filing Date
US08/501,691 Expired - Lifetime US5654345A (en) 1995-07-12 1995-07-12 In situ blown foams

Country Status (7)

Country Link
US (1) US5654345A (de)
EP (1) EP0785963A4 (de)
JP (1) JPH10505878A (de)
KR (1) KR970706341A (de)
AU (1) AU6392896A (de)
CA (1) CA2198629A1 (de)
WO (1) WO1997003115A1 (de)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001077214A2 (en) * 2000-04-06 2001-10-18 American Aerogel Corporation Organic, low density microcellular materials
US20020064642A1 (en) * 2000-04-06 2002-05-30 Albert Donald F. Organic, open cell foam materials, their carbonized derivatives, and methods for producing same
US20020114937A1 (en) * 2000-04-06 2002-08-22 Albert Donald F. Insulated barriers and methods for producing same
WO2002074842A1 (en) * 2001-03-16 2002-09-26 American Aerogel Corporation Organic, open cell foam materials,
AU2002213437B2 (en) * 2001-10-04 2008-02-21 American Aerogel Corporation Organic, open cell foam materials
CN112225869A (zh) * 2020-10-14 2021-01-15 广德祥源新材科技有限公司 一种均匀孔径聚氨酯微孔泡棉及其制备方法

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5654345A (en) * 1995-07-12 1997-08-05 Owens-Corning Fiberglas Technology, Inc. In situ blown foams

Citations (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3770671A (en) * 1972-08-14 1973-11-06 Owens Corning Fiberglass Corp Polyurethanes produced oxyalkylated resoles
US3872034A (en) * 1973-02-02 1975-03-18 Cook Paint & Varnish Co Phenolic foam
US3948824A (en) * 1972-09-08 1976-04-06 Ashland Oil, Inc. Cellular polymeric masses
US4490490A (en) * 1983-05-24 1984-12-25 Basf Wyandotte Corporation High load bearing flexible polyurethane foams
US4910231A (en) * 1987-09-21 1990-03-20 Imperial Chemical Industries Plc Manufacture of polyurethane foam
US4916168A (en) * 1987-09-21 1990-04-10 Imperial Chemical Industries Plc Manufacture of polyurethane foam
US5114989A (en) * 1990-11-13 1992-05-19 The Dow Chemical Company Isocyanate-terminated prepolymer and polyurethane foam prepared therefrom
US5130346A (en) * 1989-10-19 1992-07-14 Bridgestone Corporation Method for producing a low-density flexible polyurethane foam
US5143941A (en) * 1990-12-27 1992-09-01 Basf Corporation Energy absorbing, water blown, rigid polyurethane foam
US5166183A (en) * 1991-04-16 1992-11-24 Miles Inc. Water-blown integral skin polyurethane foams
US5167884A (en) * 1990-12-27 1992-12-01 Basf Corporation Energy absorbing, water blown, rigid polyurethane foam
US5171759A (en) * 1988-07-12 1992-12-15 Arco Chemical Technology, L.P. Polymer polyol compositions and their use in the preparation of polyurethane foams
US5177119A (en) * 1990-04-25 1993-01-05 Arco Chemical Technology, L.P. Polyurethane foams blown only with water
US5189068A (en) * 1990-06-23 1993-02-23 Basf Aktiengesellschaft Preparation of integral skin cellular plastics by the polyaddition process in the presence of tertiary alcohols
US5252625A (en) * 1990-03-19 1993-10-12 Atlas Roofing Corporation Method for producing rigid foams and products produced therefrom
US5296518A (en) * 1991-05-24 1994-03-22 Hampshire Chemical Corp. Hydrophilic polyurethaneurea foams containing no toxic leachable additives and method to produce such foams
US5328938A (en) * 1993-03-01 1994-07-12 Basf Corporation On-site generation of polyurethane foam using an HCFC as a sole blowing agent
US5432207A (en) * 1994-10-25 1995-07-11 Jiffy Foam, Inc. Phenolic foam composition and use thereof for "in place" foaming

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1268440A (en) * 1969-06-17 1972-03-29 Midwest Research Inst Method of making a foamed resin and product
EP0074064A3 (de) * 1981-09-04 1983-10-12 Toyo Rubber Chemical Industry Co. Ltd. Verfahren zur Herstellung eines Phenolharzschaumes
US5654345A (en) * 1995-07-12 1997-08-05 Owens-Corning Fiberglas Technology, Inc. In situ blown foams

Patent Citations (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3770671A (en) * 1972-08-14 1973-11-06 Owens Corning Fiberglass Corp Polyurethanes produced oxyalkylated resoles
US3948824A (en) * 1972-09-08 1976-04-06 Ashland Oil, Inc. Cellular polymeric masses
US3872034A (en) * 1973-02-02 1975-03-18 Cook Paint & Varnish Co Phenolic foam
US4490490A (en) * 1983-05-24 1984-12-25 Basf Wyandotte Corporation High load bearing flexible polyurethane foams
US4910231A (en) * 1987-09-21 1990-03-20 Imperial Chemical Industries Plc Manufacture of polyurethane foam
US4916168A (en) * 1987-09-21 1990-04-10 Imperial Chemical Industries Plc Manufacture of polyurethane foam
US5171759A (en) * 1988-07-12 1992-12-15 Arco Chemical Technology, L.P. Polymer polyol compositions and their use in the preparation of polyurethane foams
US5130346A (en) * 1989-10-19 1992-07-14 Bridgestone Corporation Method for producing a low-density flexible polyurethane foam
US5252625A (en) * 1990-03-19 1993-10-12 Atlas Roofing Corporation Method for producing rigid foams and products produced therefrom
US5177119A (en) * 1990-04-25 1993-01-05 Arco Chemical Technology, L.P. Polyurethane foams blown only with water
US5189068A (en) * 1990-06-23 1993-02-23 Basf Aktiengesellschaft Preparation of integral skin cellular plastics by the polyaddition process in the presence of tertiary alcohols
US5114989A (en) * 1990-11-13 1992-05-19 The Dow Chemical Company Isocyanate-terminated prepolymer and polyurethane foam prepared therefrom
US5167884A (en) * 1990-12-27 1992-12-01 Basf Corporation Energy absorbing, water blown, rigid polyurethane foam
US5143941A (en) * 1990-12-27 1992-09-01 Basf Corporation Energy absorbing, water blown, rigid polyurethane foam
US5166183A (en) * 1991-04-16 1992-11-24 Miles Inc. Water-blown integral skin polyurethane foams
US5296518A (en) * 1991-05-24 1994-03-22 Hampshire Chemical Corp. Hydrophilic polyurethaneurea foams containing no toxic leachable additives and method to produce such foams
US5328938A (en) * 1993-03-01 1994-07-12 Basf Corporation On-site generation of polyurethane foam using an HCFC as a sole blowing agent
US5432207A (en) * 1994-10-25 1995-07-11 Jiffy Foam, Inc. Phenolic foam composition and use thereof for "in place" foaming

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7521485B2 (en) 2000-04-06 2009-04-21 American Aerogel Corporaition Organic, open cell foam materials, their carbonized derivatives, and methods for producing same
WO2001077214A3 (en) * 2000-04-06 2002-04-04 American Aerogel Corp Organic, low density microcellular materials
US20020064642A1 (en) * 2000-04-06 2002-05-30 Albert Donald F. Organic, open cell foam materials, their carbonized derivatives, and methods for producing same
US20020114937A1 (en) * 2000-04-06 2002-08-22 Albert Donald F. Insulated barriers and methods for producing same
US8436061B2 (en) 2000-04-06 2013-05-07 American Aerogel Corporation Organic, open cell foam materials, their carbonized derivatives, and methods for producing same
US7005181B2 (en) 2000-04-06 2006-02-28 American Aerogel Corporation Organic, open cell foam materials, their carbonized derivatives, and methods for producing same
US20060079587A1 (en) * 2000-04-06 2006-04-13 American Aerogel Corporation Organic, open cell foam materials, their carbonized derivatives, and methods for producing same
US8071657B2 (en) 2000-04-06 2011-12-06 American Aerogel Corporation Organic, open cell foam materials, their carbonized derivatives, and methods for producing same
WO2001077214A2 (en) * 2000-04-06 2001-10-18 American Aerogel Corporation Organic, low density microcellular materials
US20090176085A1 (en) * 2000-04-06 2009-07-09 American Aerogel Corporation Organic, open cell foam materials, their carbonize derivatives, and methods for producing same
EP2308918A2 (de) * 2001-03-16 2011-04-13 American Aerogel Corporation Organische offenzellige Schaummaterialien
WO2002074842A1 (en) * 2001-03-16 2002-09-26 American Aerogel Corporation Organic, open cell foam materials,
EP2308918A3 (de) * 2001-03-16 2013-10-02 American Aerogel Corporation Organische offenzellige Schaummaterialien
AU2002213437C1 (en) * 2001-10-04 2008-09-04 American Aerogel Corporation Organic, open cell foam materials
AU2002213437B8 (en) * 2001-10-04 2008-03-06 American Aerogel Corporation Organic, open cell foam materials
AU2002213437B2 (en) * 2001-10-04 2008-02-21 American Aerogel Corporation Organic, open cell foam materials
CN112225869A (zh) * 2020-10-14 2021-01-15 广德祥源新材科技有限公司 一种均匀孔径聚氨酯微孔泡棉及其制备方法

Also Published As

Publication number Publication date
EP0785963A4 (de) 1998-05-06
CA2198629A1 (en) 1997-01-30
KR970706341A (ko) 1997-11-03
AU6392896A (en) 1997-02-10
EP0785963A1 (de) 1997-07-30
WO1997003115A1 (en) 1997-01-30
JPH10505878A (ja) 1998-06-09

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